Claire assures Bob that his neighbor is not spying on him. Trouble is, she's wrong.
Claire pushes the guys to try dating, until each of them meets the woman of their dreams---and then, nightmares. Meanwhile, Bob finds that he gets along a lot better with a regular gal...like his therapist.
Claire tries to get Stansfield switched to a new route after he becomes her very meddlesome mailman. Meanwhile, the rest of her patients plan a party in honor of their thoughtful therapist.
The guys try---and fail at---life without therapy after they quit Claire's group in protest of her ban on their late-night visits. But when they attempt to cure one another, Bob realizes it may be the sickest thing they've ever done.
Bob's new passion for owls lands him a lovely lady with the same taste and a feathered friend with a taste for blood. Meanwhile, Claire helps Stansfield find his hidden talents as a dancer, while facing her geeky past as a hoofer.
A big company, Xenocorp, buys Bob and Zack's building, and after a lobby party, the guys notice that there's a new surveillance camera installed, which makes them scared about being watched 24/7. So Claire tells them that it's not like that at all, and offers to call the company herself and complain about the new camera. The guys warn her about the risks of doing so, and how the company will come after her if she shows signs of dissatisfaction. Skeptical about it, Claire makes the call. When she gets home, she starts to suffer all that the guys mentioned: her apartment is suddenly available for rent, her water and heat go off, and she receives a smoked fish, which she interprets as a sign like in ""The God Father"". She decides then to go to the company herself, and unexpectedly runs into the president. He clarifies her that it was all an accident and she feels safe again.
The guys go into paranoia overdrive with the suspicion that Claire favors her other therapy group over them.
Claire advises the guys not to date anyone from the conspiracy convention they're going, trying to spare them from dating wackos. Claire's boyfriend, who she really thinks is a great guy, turns out to have a booth at the convention, and so Claire has to dump him because he's a wacko. Meanwhile, Bob is the only one who has the guts to tell Zack that he thinks his marriage is a mistake, and the two have a fight.
Zack, Bob, Max and Stansfield seek to make Claire Garletti a household name.
Zack gets a job at Bob's company, and becomes the ""office supplies pimp"" after discovering he can order whatever he wants from the catalog. He think that giving people stuff makes them like him better, and makes the guys believe it too. Bob, who was trying to flirt with his cubicle neighbor without any success, starts to give her office supplies gifts and ends up getting a lunch date. Max convinces Stansfield to try to find an old person to be friends with like he did with Doris. Incidentally, Stansfield ends up meeting the magician he liked in childhood. Max starts to give the elderly office supplies too, and they get addicted to it. Claire tells the guys that bribing people with office supplies is not a good thing, but nobody listens to her. Bob's boss comes back and finds him and Zack stealing a couch and fires them both, but Zack convinces him to keep Bob.
It's Saturday night, and everyone's got a date. That is, except for Max and Stansfield. Zack's old girlfriend, an FBI agent, ran into him and asked him out. In the morning after, Zack freaks when she starts asking questions like ""how do you like your eggs?"" and thinks she's only back with him to investigate him. On the therapy session, Claire says that sharing is an important step in the beginnings of any relationship, and if it wasn't for that, her last date wouldn't have ended in such a fiasco. Bob is very happy because he and Kristen share everything. In fact, he planned to take her on a trip to Vermont - until she tells him that Vermont reminded her of an old boyfriend and she decided to go back to him. Zack is convinced that sharing is good and apologizes to Dora. Max and Stansfield decide to spend time with each other, until they share too much.
The guys go to Claire's to ask her what she thinks about Stansfield's pants and find Lindsey, Claire's hype sister. She takes the guys to a rave party and they all wake up the next morning at Claire's. Bob finds out that he had his nipple pierced and goes to the hospital to remove it, but changes his mind after the nurse says how sexy that is. At home, he takes it off, but the nurse calls asking him out. Bob tries to keep her away from his nipple, but can't, so he gives an excuse to get out of that awkward situation. Meanwhile, Lindsey hooks up with Stansfield, who finally feels confident enough to get his own place. Bob gets body lice from an old chair at Stansfield's, and bumps into Nurse Cheryl again. Just as Stansfield finished decorating his tiny new place, Lindsey takes off and Claire is the one who has to tell Stansfield that.
Kristen is back and she tells Bob she and her old boyfriend Eric are back together. Bob plans on ""accidentally"" running into Kristen in a romantic restaurant while Max, Zack and Stansfield keep Eric busy so he doesn't show up on his date with Kristen. The guys end up having a lot of fun with Eric, and Claire runs into Bob while he waits for Kristen. Claire and Bob get to talk, and they have a ""moment"". Scared, Claire seeks for advice with her college professor; and Bob doesn't know what to do after Kristen dumps Eric to be with him. Torn between Claire and Kristen, Bob decides to get things straighten out with Claire. She decides it'll be better for them if she pretends like she felt nothing.